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Close up of chocolate whoopie pie with orange filling on a black wire rack.
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Easy Halloween Whoopie Pies

These are soft chocolate cookies sandwiched with an orange-colored cream cheese filling. A super cute Halloween bake that's great to make with kids. Top them with eyeball candies or other thematic extras.
Course Cookies
Cuisine American
Keyword halloween whoopie pies
Prep Time 20 minutes
Cook Time 10 minutes
Chilling time 20 minutes
Total Time 50 minutes
Servings 12 pies

Ingredients

Soft chocolate cookies:

  • 1 ¼ cups all-purpose flour
  • 3 tablespoons unsweetened cocoa powder
  • 1 ½ teaspoons baking soda
  • ½ teaspoon salt I like kosher salt
  • ½ cup unsalted butter at room temperature
  • ¾ cup white sugar
  • ½ cup brown sugar
  • 1 egg at room temperature
  • 1 teaspoon vanilla extract
  • ½ cup buttermilk at room temperature

Buttercream filling:

  • ½ cup unsalted butter at room temperature
  • 2 cups of powdered sugar
  • 2 tablespoons milk
  • 1-2 drops of orange gel food coloring
  • edible eyes

Instructions

  • Preheat the oven to 350°F (180°C). Line two baking sheets with parchment paper or silicone mats.

Make the chocolate cookie batter:

  • In a medium bowl, whisk together 1 ¼ cups all-purpose flour, 3 tablespoons unsweetened cocoa powder, 1 ½ teaspoons baking soda, and ½ teaspoon salt. Set aside.
  • In a large bowl, beat ½ cup unsalted butter, softened, ¾ cup white sugar, and ½ cup brown sugar with an electric mixer until light and fluffy, about 2–3 minutes.
  • Add 1 egg and 1 teaspoon vanilla extract, and beat until fully combined.
With the mixer on low speed, add the dry ingredients in two additions, alternating with ½ cup buttermilk. Begin and end with the dry ingredients, mixing just until combined. Scrape the sides of the bowl as needed. The batter should be thick but soft.

  • Drop tablespoonfuls (I use a small cookie scoop) of batter onto the prepared baking sheets, spacing them about 2 inches apart.
  • Bake for 9–11 minutes, until the tops are set and spring back lightly when touched.
  • Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Buttercream filling:

  • In a medium bowl, beat ½ cup unsalted butter, softened, until creamy. Gradually add 2 cups of powdered sugar, then 2 tablespoons milk, and beat until light and fluffy, about 2 minutes. If too soft, add a couple more tablespoons of powdered sugar. It should be thick.
  • Tint with 1-2 drops of orange gel food coloring, mixing until evenly colored.

Assemble the whoopie pies:

  • Spread or pipe a generous amount of buttercream on the flat side of one cookie. Top with another cookie to create a sandwich.
  • Press edible eyes onto the filling or on top of the cookies for a fun Halloween look.
For neater edges and firmer filling, refrigerate the assembled whoopie pies for about 20 minutes before serving, but not much longer.

Notes

Baking time: keep in mind that all ovens and pans are different, even if they look the same or very similar. The baking time in my recipes is as accurate as it can be, but it might take you more or less time. Use a thermometer inside the oven to check that the temperature is right. I recommend you keep track of how your oven works and what tiny details you might need to adjust.
Storing: soft cookies can be kept in an airtight container or jar for a few days. You can also freeze them for a month, always well wrapped. Be careful not to smash them. You can also store filled whoopies, but they will turn softer faster due to the moisture of the filling. 
How do you keep assembled whoopie pies fresh? For the freshest cakes, eat them within a day of making them. After that, keep them in an airtight container. If you fill them as you plan to eat them (a few hours ahead at the most), they will last longer without becoming soggy.
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